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    L2 - Aromatic Electrophilic Substitution PDF

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    The document provides information about electrophilic aromatic substitution reactions. It discusses the general two-step mechanism, and then covers specific reactions like halogenation, nitration, sulfonation, and Friedel-Crafts reactions. It explains the generation of electrophiles and reaction mechanisms. It also discusses limitations and examples of Friedel-Crafts reactions.

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    L2 - Aromatic Electrophilic Substitution PDF

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    101 views32 pages
    The document provides information about electrophilic aromatic substitution reactions. It discusses the general two-step mechanism, and then covers specific reactions like halogenation, nitration, sulfonation, and Friedel-Crafts reactions. It explains the generation of electrophiles and reaction mechanisms. It also discusses limitations and examples of Friedel-Crafts reactions.

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    The document provides information about electrophilic aromatic substitution reactions. It discusses the general two-step mechanism, and then covers specific reactions like halogenation, nitration, sulfonation, and Friedel-Crafts reactions. It explains the generation of electrophiles and reaction mechanisms. It also discusses limitations and examples of Friedel-Crafts reactions.

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    © All Rights Reserved
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    101 views32 pages

    L2 - Aromatic Electrophilic Substitution PDF

    Uploaded by

    Padam
    The document provides information about electrophilic aromatic substitution reactions. It discusses the general two-step mechanism, and then covers specific reactions like halogenation, nitration, sulfonation, and Friedel-Crafts reactions. It explains the generation of electrophiles and reaction mechanisms. It also discusses limitations and examples of Friedel-Crafts reactions.

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    Aromatic 11th

    Electrophilic
    Substitution
    Paaras Thakur
    Electrophilic Aromatic Substitution

    No matter what electrophile is used, all electrophilic aromatic substitution reactions occur
    via a two-step mechanism:

    The rate of reaction does not involve the breaking of C – H bond. This has been
    established by isotope effect.* The rates of reactions are the same on replacement of
    hydrogen by deuterium or tritium.
    Electrophilic Aromatic Substitution
    Halogenation

    In halogenation, benzene reacts with Cl2 or Br2 in the presence of a Lewis acid catalyst,
    such as FeCl3 or FeBr3, to give the aryl halides chlorobenzene or bromobenzene,
    respectively.

    The order of reactivity of the halogens is F2 > Cl2 > Br2 > I2. Fluorine is too reactive for
    practical use. Under ordinary condition, iodination fails. In the presence of HNO3 direct
    iodination has been effected. The attacking electrophile I is produced by HNO3.
    Halogenation Mechanism
    Nitration & Sulphonation Mechanism

    Generation of the electrophile in both nitration and sulfonation requires strong acid. In
    nitration, the electrophile is +NO2 (the nitronium ion).
    Nitration & Sulphonation Mechanism

    All of the steps in sulfonation are equilibria, which means that the overall reaction is
    reversible.

    ● If we want to sulfonate the ring (install a sulfonic acid group), we use concentrated
    sulfuric acid or—better yet—fuming sulfuric acid.

    ● If we want to de-sulfonate the ring (remove a sulfonic acid group), we employ


    dilute sulfuric acid and usually pass steam through the mixture.

    ● We sometimes install a sulfonate group as a protecting group.


    Friedel - Crafts Reactions

    In Friedel–Crafts alkylation, treatment of benzene with an alkyl halide and a Lewis acid
    (AlCl3) forms an alkyl benzene.

    In Friedel–Crafts acylation, a benzene ring is treated with an acid chloride (RCOCl) and
    AlCl3 to form a ketone.
    Friedel - Crafts Reactions Mechanism

    In Friedel–Crafts alkylation, the Lewis acid AlCl3 reacts with the alkyl chloride to form
    a Lewis acid–base complex.
    Friedel - Crafts Reactions Mechanism
    Friedel - Crafts Reactions Mechanism

    Friedel–Crafts alkylations are not restricted to the use of alkyl halides and aluminum chloride.
    Other pairs of reagents that form carbocations (or species like carbocations) may be used in
    Friedel–Crafts alkylations as well.
    Example Draw the product of each reaction.
    Example Which halides are unreactive in a Friedel–Crafts alkylation reaction?
    Friedel - Crafts Reactions Mechanism

    In Friedel–Crafts acylation, the Lewis acid AlCl3 ionizes the carbon–halogen bond of the acid
    chloride, thus forming a positively charged carbon electrophile called an acylium ion, which is
    resonance stabilized.
    Reactions
    Friedel - Crafts Reactions

    Acyl chlorides, also called acid chlorides, are easily prepared by treating carboxylic acids with
    thionyl chloride (SOCl2) or phosphorus pentachloride (PCl5):
    Friedel - Crafts Reactions Limitations

    ● In Friedel–Crafts alkylation, rearrangements are common.

    ● Friedel–Crafts reactions usually give poor yields when powerful electron-withdrawing


    groups are present on the aromatic ring or when the ring bears an -NH2, -NHR, or -NR2
    group.
    Friedel - Crafts Reactions Limitations

    ● Aryl and vinylic halides cannot be used as the halide component because they do not
    form carbocations readily.

    ● Poly-alkylations often occur in F.C. alkylation but not in acylation.


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